Effective Work Samples for Evaluating AI Chatbot Design Skills in Sales Support

AI chatbots have become essential tools in modern sales support, helping teams qualify leads, answer product questions, and move prospects through the sales funnel efficiently. However, designing effective AI chatbots for sales support requires a unique blend of technical knowledge, conversational design expertise, and understanding of sales processes. Identifying candidates with these specialized skills can be challenging through traditional interviews alone.

Work samples provide a practical way to evaluate a candidate's ability to design AI chatbots that genuinely enhance sales operations. Unlike theoretical discussions, these exercises reveal how candidates approach real-world chatbot design challenges, their understanding of sales support needs, and their technical implementation skills. The right candidate should demonstrate not just technical proficiency but also an understanding of how chatbots fit into the broader sales ecosystem.

The following work samples are designed to assess multiple dimensions of AI chatbot design for sales support. They evaluate a candidate's ability to plan chatbot architecture, create effective conversation flows, optimize existing systems, and ensure the solution meets actual sales team needs. By observing candidates complete these exercises, hiring managers can gain valuable insights into how candidates think, problem-solve, and approach the unique challenges of designing AI chatbots for sales contexts.

Implementing these exercises as part of your interview process will help you identify candidates who can not only build technically sound chatbots but also create solutions that genuinely support your sales team's objectives. The best chatbot designers combine technical skills with business acumen and user empathy—qualities these exercises are specifically designed to reveal.

Activity #1: Chatbot Conversation Flow Design

This activity assesses the candidate's ability to design effective conversational flows for sales support chatbots. A well-designed conversation flow is the foundation of any successful chatbot implementation, requiring an understanding of both user experience principles and sales processes. This exercise reveals how candidates structure conversations to guide prospects through qualification, answer product questions, and move them toward conversion.

Directions for the Company:

• Provide the candidate with a brief description of your company, key products/services, and typical sales qualification questions.
• Include information about your target audience and common customer questions or objections.
• Share examples of your current sales qualification process or conversation scripts if available.
• Allow 45-60 minutes for this exercise.
• Prepare a simple chatbot builder tool or flowchart software for the candidate to use, or accept hand-drawn diagrams if remote.

Directions for the Candidate:

• Design a conversation flow for a sales qualification chatbot that helps identify qualified leads for the sales team.
• Create a flowchart or diagram showing the conversation paths, decision points, and logic branches.
• Include at least three different conversation paths based on user responses.
• Design appropriate handoff points where the chatbot should transfer the conversation to a human sales representative.
• Prepare to explain your design decisions and how this flow supports the sales process.

Feedback Mechanism:

• After the candidate presents their design, provide feedback on one aspect they handled well (such as user experience considerations or sales qualification logic).
• Offer one specific improvement suggestion, such as an additional qualification question or a better handoff point.
• Give the candidate 10 minutes to revise their design based on this feedback and explain how their changes address the feedback.

Activity #2: Chatbot Prompt Engineering

This activity evaluates the candidate's ability to write effective prompts for large language models that power modern AI chatbots. Prompt engineering is a critical skill that determines how well the AI understands and responds to customer inquiries. This exercise reveals the candidate's technical understanding of LLMs and their ability to craft prompts that produce consistent, helpful responses in a sales context.

Directions for the Company:

• Prepare 3-5 common sales-related customer inquiries your chatbot would need to handle (e.g., pricing questions, product comparisons, feature inquiries).
• Provide information about your products/services that would be needed to answer these questions.
• If possible, provide access to a GPT or similar LLM sandbox environment for testing prompts.
• Allow 45 minutes for this exercise.

Directions for the Candidate:

• Write system prompts and example messages that would help an LLM-based chatbot respond effectively to the provided customer inquiries.
• Include context about the company, products, and sales process in your system prompt.
• Create at least one example of how to handle objections or difficult questions.
• Demonstrate how your prompts would maintain the chatbot's focus on qualifying and advancing sales opportunities.
• Test your prompts if a sandbox environment is provided and be prepared to explain your approach.

Feedback Mechanism:

• Provide feedback on one strength of the candidate's prompt engineering approach (e.g., effective context setting, good handling of edge cases).
• Suggest one improvement area, such as making the prompts more concise or adding guardrails for sensitive topics.
• Allow the candidate 10 minutes to revise one of their prompts based on your feedback and explain their changes.

Activity #3: Chatbot Integration Planning

This activity assesses the candidate's ability to plan how a sales support chatbot would integrate with existing sales systems and workflows. Successful chatbot implementation requires thoughtful integration with CRMs, sales tools, and team processes. This exercise reveals the candidate's understanding of the broader sales technology ecosystem and their ability to design solutions that enhance rather than disrupt existing workflows.

Directions for the Company:

• Provide an overview of your current sales tech stack (CRM, email tools, scheduling systems, etc.).
• Describe your current lead qualification and handoff process.
• Outline key data points collected during the sales process.
• Allow 60 minutes for this exercise.
• Provide whiteboard space or digital diagramming tools.

Directions for the Candidate:

• Create an integration plan showing how a sales support chatbot would connect with existing systems.
• Design a data flow diagram showing what information the chatbot would collect, where it would be stored, and how it would be accessed by the sales team.
• Identify key integration points with the CRM and other sales tools.
• Outline how leads would be qualified by the chatbot and transferred to the appropriate sales team members.
• Propose metrics to track the chatbot's effectiveness in supporting sales goals.

Feedback Mechanism:

• Provide feedback on one strong aspect of the integration plan (e.g., thoughtful CRM integration, good data flow design).
• Suggest one area for improvement, such as additional security considerations or a missed integration opportunity.
• Give the candidate 15 minutes to revise their plan based on this feedback and explain how their changes address the concern.

Activity #4: Chatbot Performance Optimization

This activity evaluates the candidate's ability to analyze and improve an existing chatbot's performance for sales support. Optimization is a critical ongoing process for any chatbot implementation. This exercise reveals how candidates approach problem-solving, use data to drive decisions, and balance technical improvements with business objectives.

Directions for the Company:

• Prepare a scenario describing a sales support chatbot that is underperforming in specific ways (e.g., low conversion rates, frequent handoffs to humans, customer complaints about specific topics).
• Provide sample conversation logs showing problematic interactions.
• Include basic performance metrics (completion rates, satisfaction scores, conversion rates).
• Allow 45-60 minutes for this exercise.

Directions for the Candidate:

• Analyze the provided conversation logs and metrics to identify patterns and issues.
• Develop a prioritized list of 3-5 specific improvements to address the chatbot's performance issues.
• For each recommendation, explain:
• The specific problem it addresses
• How you would implement the change
• How you would measure whether the change was successful
• Consider both technical improvements (prompt engineering, conversation flow) and business process changes.
• Prepare to present your analysis and recommendations.

Feedback Mechanism:

• Provide feedback on one strength of the candidate's analysis and recommendations (e.g., data-driven approach, creative solutions).
• Suggest one area where their approach could be improved or a consideration they might have missed.
• Allow the candidate 10 minutes to refine one of their recommendations based on your feedback and explain their reasoning.

Frequently Asked Questions

How long should we allocate for these work samples?

Each exercise is designed to take 45-60 minutes. For remote interviews, consider sending the preparation materials ahead of time and focusing the interview on presentation and discussion. For on-site interviews, you might select just 1-2 exercises rather than attempting all four.

Should candidates have access to AI tools during these exercises?

For the prompt engineering exercise, access to an LLM sandbox is ideal but not required. For other exercises, basic tools like flowcharting software or whiteboarding tools are sufficient. The focus should be on design thinking and problem-solving rather than technical implementation.

How technical should candidates be to complete these exercises?

These exercises focus more on design thinking and understanding of conversational AI principles rather than coding or development skills. Candidates should understand how LLMs work and basic principles of prompt engineering, but deep technical expertise is only necessary if the role involves actual development.

How can we adapt these exercises for different levels of seniority?

For junior roles, focus on the conversation flow design and prompt engineering exercises with more guidance provided. For senior roles, emphasize the integration planning and performance optimization exercises, and expect more strategic thinking about how the chatbot supports broader business goals.

What if we don't currently use chatbots in our sales process?

These exercises can still be valuable. Frame them as exploratory exercises to understand how chatbots might enhance your current process. Ask candidates to consider your specific sales context and design solutions that would address your unique challenges.

How should we evaluate candidates who take different approaches to these exercises?

Focus on the reasoning behind their decisions rather than expecting a specific "right answer." Strong candidates should be able to explain their design choices, demonstrate understanding of sales processes, and show how their solutions would support business objectives, even if their approach differs from what you might have expected.

Finding the right talent to design AI chatbots for sales support can significantly impact your team's efficiency and effectiveness. These work samples provide a structured way to evaluate candidates' practical skills and approach to chatbot design challenges. By implementing these exercises in your hiring process, you'll be better equipped to identify candidates who can create chatbot solutions that genuinely enhance your sales operations.

For more resources to improve your hiring process, check out Yardstick's AI Job Descriptions, AI Interview Question Generator, and AI Interview Guide Generator. These tools can help you create comprehensive interview processes that identify the best talent for your specific needs.

Build a complete interview guide for AI Chatbot Design roles by signing up for a free Yardstick account